The 1999 interview between Conan O’Brien and actress Kari Wuhrer on Late Night has gone down as one of the most awkward moments in late-night TV history. It’s a rare example where the charm of the host, usually quick-witted and confident, seemed to falter under the weight of some uncomfortable exchanges.
Wuhrer, known at the time for her roles in shows like Sliders and films such as Anaconda, appeared on the show promoting her work. But from the start, the interview felt off. There was an odd tension between the two, partly sparked by some clumsy attempts at flirtation and jokes that didn’t land. The natural rhythm you expect in a talk show was missing. Instead, it became a bit of a stilted back-and-forth, with both trying to find footing but not quite succeeding.
Conan’s usual humour, which often diffuses awkwardness, seemed to only heighten the discomfort. Meanwhile, Wuhrer’s responses came across as guarded and occasionally defensive, as if she wasn’t sure how to handle the situation. Some viewers have pointed out how the awkwardness might have been amplified by the live audience, making it harder for both to relax.
Looking back, the interview feels like a snapshot of a moment where things just didn’t click. It’s become a sort of cult classic among late-night fans, watched both for cringe and for the human side it shows behind the polished facade of television interviews. Everyone has an off day, and this one just happened to be on camera for all to see.
